Levcromakalim

Base Information

• Chemical Name: Levcromakalim
• CAS No.: 94535-50-9
• Molecular Formula: C₁₆H₁₈N₂O₃
• Molecular Weight: 286.331
• Hs Code.: 2934999090
• UNII: RW7PN4BLDJ,0G4X367WA3
• DSSTox Substance ID: DTXSID5045677
• Nikkaji Number: J257.580I
• Wikipedia: Cromakalim
• Wikidata: Q76009683
• NCI Thesaurus Code: C79109,C91002
• Metabolomics Workbench ID: 68020
• ChEMBL ID: CHEMBL100
• Mol file: 94535-50-9.mol

Synonyms:BRL 38226;BRL 38227;BRL-34915;BRL-38226;BRL-38227;BRL38226;BRL38227;Cromakalim;Cromakalim, (3R-cis)-Isomer;Cromakalim, (3R-trans)-Isomer;Cromakalim, (3S-cis)-Isomer;Cromakalim, (3S-trans)-Isomer;Cromakalim, (trans)-Isomer;Lemakalim;Levcromakalim

Chemical Property of Levcromakalim

Chemical Property:

• Melting Point: 242-244°
• Boiling Point: 482.3°Cat760mmHg
• PKA: 13.18±0.60(Predicted)
• Flash Point: 245.5°C
• PSA: 73.56000
• Density: 1.31g/cm³
• LogP: 1.69158
• Storage Temp.: Store at RT
• Solubility.: DMSO: ≤10 mM, soluble
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 286.13174244
• Heavy Atom Count: 21
• Complexity: 481

Purity/Quality:

97% ^*data from raw suppliers

Levcromakalim ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C(C2=C(O1)C=CC(=C2)C#N)N3CCCC3=O)O)C
• Isomeric SMILES: CC1([C@H]([C@@H](C2=C(O1)C=CC(=C2)C#N)N3CCCC3=O)O)C
• Recent ClinicalTrials: Migraine Inducing Effect of Levcromakalim in Patients With Migraine With Aura
• Uses: Anti-asthmatic; antihypertensive. Levcromakalim is a potassium channel activator and vasorelaxant used in the management of hypertension in diabetes mellitus.

Technology Process of Levcromakalim

There total 10 articles about Levcromakalim which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

(3S,4R)-3-methoxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)chroman-6-carbonitrile → Levcromakalim (94535-50-9,148811-94-3)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.151431

Reference yield: 62.0%

2-pyrrolidinon (616-45-5) + 6-cyano-2,2-dimethylchromene-3,4-epoxide (65018-90-8,75611-72-2,114926-02-2,114926-03-3) → Levcromakalim (94535-50-9,148811-94-3)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; mineral oil; at 20 ℃;

Reference yield:

6-cyano-2,2-dimethylchromene (33143-29-2) → Levcromakalim (94535-50-9,148811-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / chiral dihydroisoquinolinium salt; tetraphenylphosphonium monoperoxysulfate / CHCl₃ / 24 h / -40 °C

2: 52 percent / NaH / dimethylsulfoxide / 6 h

With chiral dihydroisoquinolinium salt; sodium hydride; tetraphenylphosphonium monoperoxysulfate; In chloroform; dimethyl sulfoxide;

DOI:10.1021/ol047836h

upstream raw materials:

2-pyrrolidinon

6-cyano-2,2-dimethylchromene-3,4-epoxide

6-cyano-2,2-dimethylchromene

cromakalim